Deals on vacations and trips to Winchester

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Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 3 conference rooms, free WiFi in public areas, and laundry service. Enjoy the free continental breakfast each morning.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
Holly Tree Resort

Holly Tree Resort

3 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features an indoor pool and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.

Top Winchester hotels deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
Get rates
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.
Pool
Spa
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St, Boston, MA
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, express check-in, and express check-out are also offered.
Free WiFi
Restaurant
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

4 out of 5
47 Huntington Ave, Boston, MA
Free Cancellation
Reserve now, pay when you stay
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A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, express check-out, and luggage storage are also offered.
Free WiFi
Restaurant
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
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A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.
Free WiFi
Restaurant
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.
Pet friendly
Free WiFi
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street, Boston, MA
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.
Pet friendly
Restaurant
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(1,966 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Frequently asked questions

How much are vacation packages to Winchester?
Treat yourself to a memorable travel experience in Winchester with a vacation package starting at just $696. Reserving your flights, hotels and tours with Travelocity is so simple. And even better, our great deals will leave you with extra cash for fun.
Where can I get the best vacation package deals for Winchester?
You can pick up awesome Winchester package deals with Travelocity. Select from as many as 400 partner airlines and 1,000,000 properties worldwide and turn your travel dreams into reality.
Why should I purchase my Winchester vacation package via Travelocity?
You’ll not only enjoy big savings, but you’ll also have access to our 24/7 support, high-quality service and a Price Match Guarantee. Wander across the world, discover hidden sights and make lifelong memories — we’ll take care of the important details.
Can I save on my Winchester car rental if I bundle it with hotels and flights?
Combining your hotel, flight and car into a Winchester vacation package is the easiest way to land the best deal. Plus, having your own rental car gives you freedom to get to all those famous sights you want to see. Sitting 40 mi away from Winchester, Plymouth Rock is one attraction that should be on your itinerary. Buckle up and make a day trip of it.
Which airport is best for Winchester?
Many people fly into Logan Intl. Airport (BOS), 9 mi southeast of downtown Winchester. Others prefer T.F. Green Airport (PVD) (55 mi away from central Winchester) or Manchester-Boston Regional Airport (MHT) (35 mi away from central Winchester).
What is there to do in Winchester?
Snap up the excellent photo-ops at Winter Pond, one of the most well-known attractions in Winchester. There’s plenty more to uncover in this exciting destination, so give yourself enough time to visit some of its hidden gems.
Where should I stay when visiting Winchester?
Many people spend their nights at the Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93. It’s sure to be a good base for your Winchester getaway.

Photos of local treasures

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